diff --git a/docs/src/rules/no-extra-parens.md b/docs/src/rules/no-extra-parens.md
index 8e5bb714cbd..9b1b8df0725 100644
--- a/docs/src/rules/no-extra-parens.md
+++ b/docs/src/rules/no-extra-parens.md
@@ -38,6 +38,7 @@ This rule has an object option for exceptions to the `"all"` option:
 * `"enforceForSequenceExpressions": false` allows extra parentheses around sequence expressions
 * `"enforceForNewInMemberExpressions": false` allows extra parentheses around `new` expressions in member expressions
 * `"enforceForFunctionPrototypeMethods": false` allows extra parentheses around immediate `.call` and `.apply` method calls on function expressions and around function expressions in the same context.
+* `"allowParensAfterCommentPattern": "any-string-pattern"` allows extra parentheses preceded by a comment that matches a regular expression.
 
 ### all
 
@@ -322,6 +323,34 @@ const quux = (function () {}.apply());
 
 :::
 
+### allowParensAfterCommentPattern
+
+To make this rule allow extra parentheses preceded by specific comments, set this option to a string pattern that will be passed to the [`RegExp` constructor](https://developer.mozilla.org/en-US/docs/Web/JavaScript/Reference/Global_Objects/RegExp/RegExp).
+
+Examples of **correct** code for this rule with the `"all"` and `{ "allowParensAfterCommentPattern": "@type" }` options:
+
+::: correct
+
+```js
+/* eslint no-extra-parens: ["error", "all", { "allowParensAfterCommentPattern": "@type" }] */
+
+const span = /**@type {HTMLSpanElement}*/(event.currentTarget);
+
+if (/** @type {Foo | Bar} */(options).baz) console.log('Lint free');
+
+foo(/** @type {Bar} */ (bar), options, {
+    name: "name",
+    path: "path",
+});
+
+if (foo) {
+    /** @type {Bar} */
+    (bar).prop = false;
+}
+```
+
+:::
+
 ### functions
 
 Examples of **incorrect** code for this rule with the `"functions"` option:
diff --git a/lib/rules/no-extra-parens.js b/lib/rules/no-extra-parens.js
index 246a5a0d5e1..75ac606ea74 100644
--- a/lib/rules/no-extra-parens.js
+++ b/lib/rules/no-extra-parens.js
@@ -52,7 +52,8 @@ module.exports = {
                                 enforceForArrowConditionals: { type: "boolean" },
                                 enforceForSequenceExpressions: { type: "boolean" },
                                 enforceForNewInMemberExpressions: { type: "boolean" },
-                                enforceForFunctionPrototypeMethods: { type: "boolean" }
+                                enforceForFunctionPrototypeMethods: { type: "boolean" },
+                                allowParensAfterCommentPattern: { type: "string" }
                             },
                             additionalProperties: false
                         }
@@ -86,6 +87,7 @@ module.exports = {
             context.options[1].enforceForNewInMemberExpressions === false;
         const IGNORE_FUNCTION_PROTOTYPE_METHODS = ALL_NODES && context.options[1] &&
             context.options[1].enforceForFunctionPrototypeMethods === false;
+        const ALLOW_PARENS_AFTER_COMMENT_PATTERN = ALL_NODES && context.options[1] && context.options[1].allowParensAfterCommentPattern;
 
         const PRECEDENCE_OF_ASSIGNMENT_EXPR = precedence({ type: "AssignmentExpression" });
         const PRECEDENCE_OF_UPDATE_EXPR = precedence({ type: "UpdateExpression" });
@@ -402,6 +404,19 @@ module.exports = {
                 if (isIIFE(node) && !isParenthesised(node.callee)) {
                     return;
                 }
+
+                if (ALLOW_PARENS_AFTER_COMMENT_PATTERN) {
+                    const commentsBeforeLeftParenToken = sourceCode.getCommentsBefore(leftParenToken);
+                    const totalCommentsBeforeLeftParenTokenCount = commentsBeforeLeftParenToken.length;
+                    const ignorePattern = new RegExp(ALLOW_PARENS_AFTER_COMMENT_PATTERN, "u");
+
+                    if (
+                        totalCommentsBeforeLeftParenTokenCount > 0 &&
+                        ignorePattern.test(commentsBeforeLeftParenToken[totalCommentsBeforeLeftParenTokenCount - 1].value)
+                    ) {
+                        return;
+                    }
+                }
             }
 
             /**
diff --git a/tests/lib/rules/no-extra-parens.js b/tests/lib/rules/no-extra-parens.js
index 96ae9f5bddf..3f57e5b2958 100644
--- a/tests/lib/rules/no-extra-parens.js
+++ b/tests/lib/rules/no-extra-parens.js
@@ -738,8 +738,39 @@ ruleTester.run("no-extra-parens", rule, {
         },
         {
             code: "(Object.prototype.toString.call())",
-            options: ["functions"],
-            parserOptions: { ecmaVersion: 2020 }
+            options: ["functions"]
+        },
+
+        // "allowParensAfterCommentPattern" option
+        {
+            code: "const span = /**@type {HTMLSpanElement}*/(event.currentTarget);",
+            options: ["all", { allowParensAfterCommentPattern: "@type" }]
+        },
+        {
+            code: "if (/** @type {Compiler | MultiCompiler} */(options).hooks) console.log('good');",
+            options: ["all", { allowParensAfterCommentPattern: "@type" }]
+        },
+        {
+            code: `
+                validate(/** @type {Schema} */ (schema), options, {
+                    name: "Dev Server",
+                    baseDataPath: "options",
+                });
+            `,
+            options: ["all", { allowParensAfterCommentPattern: "@type" }]
+        },
+        {
+            code: `
+                if (condition) {
+                    /** @type {ServerOptions} */
+                    (options.server.options).requestCert = false;
+                }
+            `,
+            options: ["all", { allowParensAfterCommentPattern: "@type" }]
+        },
+        {
+            code: "const net = ipaddr.parseCIDR(/** @type {string} */ (cidr));",
+            options: ["all", { allowParensAfterCommentPattern: "@type" }]
         }
     ],
 
@@ -3192,6 +3223,160 @@ ruleTester.run("no-extra-parens", rule, {
             errors: [{ messageId: "unexpected" }]
         },
 
+        // "allowParensAfterCommentPattern" option (off by default)
+        {
+            code: "const span = /**@type {HTMLSpanElement}*/(event.currentTarget);",
+            output: "const span = /**@type {HTMLSpanElement}*/event.currentTarget;",
+            options: ["all"],
+            errors: [{ messageId: "unexpected" }]
+        },
+        {
+            code: "if (/** @type {Compiler | MultiCompiler} */(options).hooks) console.log('good');",
+            output: "if (/** @type {Compiler | MultiCompiler} */options.hooks) console.log('good');",
+            options: ["all"],
+            errors: [{ messageId: "unexpected" }]
+        },
+        {
+            code: `
+                validate(/** @type {Schema} */ (schema), options, {
+                    name: "Dev Server",
+                    baseDataPath: "options",
+                });
+            `,
+            output: `
+                validate(/** @type {Schema} */ schema, options, {
+                    name: "Dev Server",
+                    baseDataPath: "options",
+                });
+            `,
+            options: ["all"],
+            errors: [{ messageId: "unexpected" }]
+        },
+        {
+            code: `
+                if (condition) {
+                    /** @type {ServerOptions} */
+                    (options.server.options).requestCert = false;
+                }
+            `,
+            output: `
+                if (condition) {
+                    /** @type {ServerOptions} */
+                    options.server.options.requestCert = false;
+                }
+            `,
+            options: ["all"],
+            errors: [{ messageId: "unexpected" }]
+        },
+        {
+            code: "const net = ipaddr.parseCIDR(/** @type {string} */ (cidr));",
+            output: "const net = ipaddr.parseCIDR(/** @type {string} */ cidr);",
+            options: ["all"],
+            errors: [{ messageId: "unexpected" }]
+        },
+        {
+            code: "const span = /**@type {HTMLSpanElement}*/(event.currentTarget);",
+            output: "const span = /**@type {HTMLSpanElement}*/event.currentTarget;",
+            options: ["all", { allowParensAfterCommentPattern: "invalid" }],
+            errors: [{ messageId: "unexpected" }]
+        },
+        {
+            code: "if (/** @type {Compiler | MultiCompiler} */(options).hooks) console.log('good');",
+            output: "if (/** @type {Compiler | MultiCompiler} */options.hooks) console.log('good');",
+            options: ["all", { allowParensAfterCommentPattern: "invalid" }],
+            errors: [{ messageId: "unexpected" }]
+        },
+        {
+            code: `
+                validate(/** @type {Schema} */ (schema), options, {
+                    name: "Dev Server",
+                    baseDataPath: "options",
+                });
+            `,
+            output: `
+                validate(/** @type {Schema} */ schema, options, {
+                    name: "Dev Server",
+                    baseDataPath: "options",
+                });
+            `,
+            options: ["all", { allowParensAfterCommentPattern: "invalid" }],
+            errors: [{ messageId: "unexpected" }]
+        },
+        {
+            code: `
+                if (condition) {
+                    /** @type {ServerOptions} */
+                    (options.server.options).requestCert = false;
+                }
+            `,
+            output: `
+                if (condition) {
+                    /** @type {ServerOptions} */
+                    options.server.options.requestCert = false;
+                }
+            `,
+            options: ["all", { allowParensAfterCommentPattern: "invalid" }],
+            errors: [{ messageId: "unexpected" }]
+        },
+        {
+            code: `
+                if (condition) {
+                    /** @type {ServerOptions} */
+                    /** extra coment */
+                    (options.server.options).requestCert = false;
+                }
+            `,
+            output: `
+                if (condition) {
+                    /** @type {ServerOptions} */
+                    /** extra coment */
+                    options.server.options.requestCert = false;
+                }
+            `,
+            options: ["all", { allowParensAfterCommentPattern: "@type" }],
+            errors: [{ messageId: "unexpected" }]
+        },
+        {
+            code: `
+                if (condition) {
+                    /** @type {ServerOptions} */
+                    ((options.server.options)).requestCert = false;
+                }
+            `,
+            output: `
+                if (condition) {
+                    /** @type {ServerOptions} */
+                    (options.server.options).requestCert = false;
+                }
+            `,
+            options: ["all", { allowParensAfterCommentPattern: "@type" }],
+            errors: [{ messageId: "unexpected" }]
+        },
+        {
+            code: `
+                if (condition) {
+                    /** @type {ServerOptions} */
+                    let foo = "bar";
+                    (options.server.options).requestCert = false;
+                }
+            `,
+            output: `
+                if (condition) {
+                    /** @type {ServerOptions} */
+                    let foo = "bar";
+                    options.server.options.requestCert = false;
+                }
+            `,
+            options: ["all", { allowParensAfterCommentPattern: "@type" }],
+            errors: [{ messageId: "unexpected" }]
+        },
+        {
+            code: "const net = ipaddr.parseCIDR(/** @type {string} */ (cidr));",
+            output: "const net = ipaddr.parseCIDR(/** @type {string} */ cidr);",
+            options: ["all", { allowParensAfterCommentPattern: "invalid" }],
+            errors: [{ messageId: "unexpected" }]
+        },
+
         // Optional chaining
         {
             code: "var v = (obj?.aaa)?.aaa",